TEMPO-Based Ionic Liquid with Temperature-Dependent Property and Application for Aerobic Oxidation of Alcohols

REFERENCES

• Hudlicky , M. Oxidations in Organic Chemistry ; American Chemical Society : Washington , DC , 1990 .
   Google Scholar
• Choudhary , V. R. ; Chaudhari , P. A. ; Narkhede , V. S. Solvent-free liquid-phase oxidation of benzyl alcohol to benzaldehyde by molecular oxygen using non-noble transition metal containing hydrotalcite-like solid catalysts . Catal. Commun. 2003 , 4 , 171 – 175 .
   Web of Science ®Google Scholar
• Cella , J. A. ; Kelley , J. A. ; Kenehan , E. F. Nitroxide-catalyzed oxidation of alcohols using m-chloroperbenzoic acid: New method . J. Org. Chem. 1975 , 40 , 1860 – 1862 .
   Web of Science ®Google Scholar
• Rychovsky , S. D. ; Vaidyanathan , R. TEMPO-catalyzed oxidations of alcohols using m-CPBA: The role of halide ions . J. Org. Chem. 1999 , 64 , 310 – 312 .
   PubMed Web of Science ®Google Scholar
• Anelli , P. L. ; Biffi , C. ; Montanari , F. ; Quici , S. J. Catalytic reactions of metalloporphyrins, 3: Catalytic modification of hydroboration-oxidation of olefins with rhodium(III) porphyrin as catalyst . J. Org. Chem. 1987 , 52 , 2559 – 2562 .
   Web of Science ®Google Scholar
• Semmelhack , M. F. ; Schmid , C. R. ; Cortés , D. A. ; Chou , C. S. Oxidation of alcohols to aldehydes with oxygen and cupric ion, mediated by nitrosonium ion . J. Am. Chem. Soc. 1984 , 106 , 3374 – 3376 .
   Web of Science ®Google Scholar
• Ciriminna , R. ; Pagliaro , M. Industrial oxidations with organocatalyst TEMPO and its derivatives . Org. Process Res. Dev. 2009 , 14 , 245 – 251 .
   Web of Science ®Google Scholar
• Hossain , M. M. ; Shyu , S. G. Efficient and selective aerobic alcohol oxidation catalyzed by copper(II)/2,2,6,6,-tetramethylpiperidine-1-oxyl at room temperature . Adv. Synth. Catal. 2010 , 352 , 3061 – 3068 .
   Web of Science ®Google Scholar
• Benaglia , M. ; Puglisi , A. ; Holczknecht , O. ; Quici , S. ; Pozzi , G. Aerobic oxidation of alcohols to carbonyl compounds mediated by poly(ethylene glycol)–supported TEMPO radicals. Tetrahedron 2005, 61, 12058–12064.
   Web of Science ®Google Scholar
• Pozzi , G. ; Cavazzini , M. ; Quici , S. ; Benaglia , M. ; Dell'Anna , G. Poly(ethylene glycol)–supported TEMPO: An efficient, recoverable metal-free catalyst for the selective oxidation of alcohols . Org. Lett. 2004 , 6 , 441 – 443 .
   PubMed Web of Science ®Google Scholar
• Bolm , C. ; Magnus , A. S. ; Hildebrand , J. P. Catalytic synthesis of aldehydes and ketones under mild conditions using TEMPO/oxone . Org. Lett. 2000 , 2 , 1173 – 1175 .
   PubMed Web of Science ®Google Scholar
• Bolm , C. ; Fey , T. TEMPO oxidations with a silica-supported catalyst . Chem. Commun. 1999 , 1795 – 1796 .
   Web of Science ®Google Scholar
• Fey , T. ; Fischer , H. ; Bachmann , S. ; Albert , K. ; Bolm , C. Silica-supported TEMPO catalysts: Synthesis and application in the Anelli oxidation of alcohols . J. Org. Chem. 2001 , 66 , 8154 – 8159 .
   PubMed Web of Science ®Google Scholar
• Verhoef , M. ; Peters , J. ; van Bekkum , H. MCM-41-supported TEMPO as an environmentally friendly catalyst in alcohol oxidation . Stud. Surf. Sci. Catal. 1999 , 125 , 465 – 472 .
   Google Scholar
• Brunel , D. ; Fajula , F. ; Nagy , J. ; Deroide , B. ; Verhoef , M. ; Veum , L. ; Peters , J. ; van Bekkum , H. Comparison of two MCM-41-grafted TEMPO catalysts in selective alcohol oxidation . Appl. Catal. A. 2001 , 213 , 73 – 82 .
   Web of Science ®Google Scholar
• Ciriminna , R. ; Blum , J. ; Avnir , D. ; Pagliaro , M. Sol-gel-entrapped TEMPO for the selective oxidation of methyl α -D-glucopyranoside . Chem. Commun. 2000 , 1441 – 1442 .
   Web of Science ®Google Scholar
• Ciriminna , R. ; Bolm , C. ; Fey , T. ; Pagliaro , M. Sol-gel ormosils doped with TEMPO as recyclable catalysts for the selective oxidation of alcohols . Adv. Synth. Catal. 2002 , 344 , 159 – 163 .
   Web of Science ®Google Scholar
• Dijksman , A. ; Arends , I. Polymer-immobilised TEMPO (PIPO): An efficient catalyst for the chlorinated hydrocarbon solvent-free and bromide-free oxidation of alcohols with hypochlorite . Chem. Commun. 2000 , 271 – 272 .
   Web of Science ®Google Scholar
• Luo , J. ; Pardin , C. ; Lubell , W. D. ; Zhu , X. X. Poly(vinyl alcohol)-graft-poly(ethylene glycol) resins and their use in solid-phase synthesis and supported TEMPO catalysis . Chem. Commun. 2007 , 2136 – 2138 .
   PubMed Web of Science ®Google Scholar
• Miao , C. X. ; He , L. N. ; Wang , J. Q. ; Wang , J. L. TEMPO and carboxylic acid functionalized imidazolium salts/sodium nitrite: An efficient, reusable, transition-metal-free catalytic system for aerobic oxidation of alcohols . Adv. Synth. Catal. 2009 , 351 , 2209 – 2216 .
   Web of Science ®Google Scholar
• Miao , C. X. ; He , L. N. ; Wang , J. L. ; Wu , F. Self-neutralizing in situ acidic CO2/H2O system for aerobic oxidation of alcohols catalyzed by TEMPO functionalized imidazolium salt/NaNO2 . J. Org. Chem. 2010 , 75 , 257 – 260 .
   PubMed Web of Science ®Google Scholar
• Miao , C. X. ; Wang , J. Q. ; Yu , B. ; Cheng , W. G. ; Sun , J. A. ; Chanfreau , S. ; He , L. N. ; Zhang , S. J. Synthesis of bimagnetic ionic liquid and application for selective aerobic oxidation of aromatic alcohols under mild conditions . Chem. Commun. 2011 , 47 , 2697 – 2699 .
   PubMed Web of Science ®Google Scholar
• Fall , A. ; Sene , M. ; Gaye , M. ; Gómez , G. ; Fall , Y. Ionic-liquid-supported TEMPO as catalyst in the oxidation of alcohols to aldehydes and ketones . Tetrahedron Lett. 2010 , 51 , 4501 – 4504 .
   Web of Science ®Google Scholar
• Tan , B. ; Jiang , J. Y. ; Wang , Y. H. ; Wei , L. ; Chen , D. J. ; Jin , Z. L. Thermoregulated ionic liquids and their application for the hydroformylation of 1-dodecene catalyzed by Rh/TPPTS complex . Appl. Organomet. Chem. 2008 , 22 , 620 – 623 .
   Web of Science ®Google Scholar
• van den Broeke , J. ; Winter , F. ; Deelman , B. J. ; van Koten , G. A highly fluorous room-temperature ionic liquid exhibiting fluorous biphasic behavior and its use in catalyst recycling . Org. Lett. 2002 , 4 , 3851 – 3854 .
   PubMed Web of Science ®Google Scholar
• Zhi , H. ; Lu , C. ; Zhang , Q. ; Luo , J. A new PEG-1000-based dicationic ionic liquid exhibiting temperature-dependent phase behavior with toluene and its application in one-pot synthesis of benzopyrans . Chem. Commun. 2009 , 00 , 2878 – 2880 .
   Web of Science ®Google Scholar
• Fang , C. ; Hang , Y. ; Jiang , J. ; Yang , Y. ; Yu , F. ; Jin , Z. Using thermoregulated PEG biphase system to effect the hydroformylation of p-isobutylstyrene catalyzed by Rh/OPGPP complex. J. Mol. Catal. A: Chem. 2006, 248, 159–162.
   Web of Science ®Google Scholar
• Miao , C. X. ; He , L. N. ; Wang , J. Q. ; Gao , J. Biomimetic oxidation of alcohols catalyzed by TEMPO-functionalized polyethylene glycol and copper(I) chloride in compressed carbon dioxide . Synlett. 2009 , 20 , 3291 – 3294 .
   Google Scholar
• Ferreira , P. ; Phillips , E. ; Rippon , D. ; Tsang , S. C. ; Hayes , W. Poly(ethylene glycol)-supported nitroxyls: Branched catalysts for the selective oxidation of alcohols . J. Org. Chem. 2004 , 69 , 6851 – 6859 .
   PubMed Web of Science ®Google Scholar
• Liu , R. H. ; Liang , X. M. ; Dong , C. Y. ; Hu , X. Q. Transition-metal-free: A highly efficient catalytic aerobic alcohol oxidation process . J. Am. Chem. Soc. 2004 , 126 , 4112 – 4113 .
   PubMed Web of Science ®Google Scholar
• He , X. J. ; Shen , Z. L. ; Mo , W. M. ; Sun , N. ; Hu , B. X. ; Hu , X. Q. TEMPO-tert-butyl nitrite: an efficient catalytic system for aerobic oxidation of alcohols . Adv. Synth. Catal. 2009 , 351 , 89 – 92 .
   Web of Science ®Google Scholar